Mobsters and Haunted Mysteries of Chicago Walking Tour
Fight and fright in the Windy City
$34 per adult
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Local experts
Personal stories and insider travel tips -
Top-rated
Thousands of reviews averaging 4.9 stars -
Worry-free booking
Flexible scheduling and refunds
$34 per adult
$34 per adult
-
Local experts
Personal stories and insider travel tips -
Top-rated
Thousands of reviews averaging 4.9 stars -
Worry-free booking
Flexible scheduling and refunds
Highlights
- Visit the favorite hangouts of Chicago’s most infamous gangsters.
- Walk the streets and alleyways that once hummed with illicit activity.
- Hear the ghostly story of the hitchhiking flapper girl who roams the roads as you walk by the start of the legendary Route 66.
- Feel the echoes of departed souls as you stand atop of the remains of the Great Chicago Fire.
- Learn how mobsters used Lake Michigan as their dumping grounds — and for what.
What you'll do
As the sun sets on Chicago’s Magnificent Mile, you’ll walk with the spirits of gangsters and condemned ghosts through the alleys, waterways, backstreets, and famous landmarks of the city.
If you love history, true crime, and spooky ...
As the sun sets on Chicago’s Magnificent Mile, you’ll walk with the spirits of gangsters and condemned ghosts through the alleys, waterways, backstreets, and famous landmarks of the city.
If you love history, true crime, and spooky mysteries, this is the tour for you! On this haunted Chicago walking tour, you’ll hear harrowing tales of how mobsters once ruled the city, ghost stories about historical events and figures, and much more.
Each tour is led by an expert guide with a passion for this city’s unique legacy. Whether you’re visiting Chicago for the first time or have lived here your whole life, this tour’s spine-tingling tales offer exhilarating thrills and chills. Join us as we uncover some of Chicago’s darkest secrets.
Itinerary
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Congress Plaza Hotel
Considered the most haunted hotel in America
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Exchequer Restaurant AKA the 226 Club
Al Capone’s favorite hangout
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Under the “L”
Once a hotbed of crime and vice
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Alley of Death
Known for strange and supernatural activity
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Chicago River
A scenic waterway of age-old tragedy
Plan your trip
Tour ending point
This tour ends near N. Michigan Avenue and Wacker Drive.
Refund policy
We offer a 100% refund up to 24 hours before the start time.
Reviews
Took the Mobs and Haunts Walking Tour with Ben, who made it really worth it despite the intense cold. Ben is full of interesting facts and anecdotes about Chicago. I totally recommend it!
— Andres
Aneta
Lauren
Meeting point
Meet your tour guide in front of the Congress Plaza Hotel & Convention Center. The hotel address is 520 S. Michigan Ave, Chicago, IL 60605.
FAQs
How much walking is there?
This tour covers about 1.5 miles at a leisurely pace.
What is the rescheduling policy?
We understand plans change. We offer a 100% refund or the option to reschedule up to 24 hours prior to your tour start time. Within 24 hours of your tour, we would have incurred hard costs and therefore cannot allow rescheduling or cancellation without costs.
When should I get there?
Plan to show up 15 minutes early. The tour starts promptly, and you may not be able to catch up if you arrive late.
What if it rains?
Our tours run rain or shine. If there’s extreme weather and we have to cancel, you’ll get a full refund.
Are gratuities included?
Tips aren’t included but are always appreciated by our guides. If you think your guide did an outstanding job, a tip is a great way to show that.
